Old Town, Alexandria, VA

I visit Old Town almost as often as I visit Georgetown. Though Old Town is a bit further away, for some reason it feels more accessible and less chaotic - there is far less shopping, but King Street is much more walkable because you aren’t having to fight for space with an army of tourists. I also adore the character of the homes to the North and South of King Street, and could spend hours wandering along them. As you are strolling, be sure to check out Mason & Greens as well as Penny Post and Red Barn Mercantile - boutiques such as these feel few and far between near DC, so I make a point to go out of my way to visit these shops at least once a season.

Leesburg, VA

At this present moment, Leesburg might be my top recommendation for a DC daytrip – it’s about an hour away, so you will really feel as though you’ve left the city, and there is just the right amount of things to do for a long afternoon. A visit around the holidays is particularly magical, and a visit to Lucketts is an absolute must for their holiday open house (truly, this might be the closest you can get to the North Pole). Wldwst and Buford’s Biscuits were also standouts during my visit.

Frederick, MD

Frederick was another pleasant surprise - I visited with fairly low expectations, but left completely charmed. You could make a day, if not a quick weekend, out of a trip to Frederick, especially if you are on the hunt for some good antiques. Though North Market Street is the main retail drag, unlike some of the other small cities I’ve explored, there is some quality retail worth straying from the beaten path for, such as Great Stuff by Paul, Relish Decor, and Emporium Antiques. I made an afternoon trip of it during the peak of fall and can say with confidence that my time there was truly delightful, and if I could have done anything different, I would have stayed for a drink at Attaboy Beer.

Middleburg, VA

I expected Middleburg to be be about the same size of the other quaint, Virginian towns I had visited, and though it was quaint, it was much, much smaller than I anticipated. A part of me was left thinking, did I miss something? It is absolutely worth a trip if you are planning to visit a vineyard or two, relax at the hotel (might I recommend the lovely Red Fox Inn?), and then spend a slow Sunday morning antiquing, but I would not recommend if you enjoy wandering through shops and neighborhoods for hours on end, with the expectation that you’ll log 12 miles by the end of the day (my typical approach, for better or for worse). To make the most of your time there, be sure to visit the neighboring Upperville as well, and have lunch or dinner at the delicious Hunter’s Head Tavern.